Here, we present a strategy for the synthesis of rotaxane-type derivatives of carbon nanotubes, the first example of mechanically interlocked derivatives of SWNTs (MINTs).¹ In the key rotaxane-forming step, we employed macrocycle precursors equipped with two recognition units and terminated with bisalkenes that were closed around the nanotubes through ring-closing metathesis (RCM). The mechanically interlocked nature of the derivatives is probed by analytical, spectroscopic, and microscopic techniques, as well as by appropriate control experiments. Remarkably, bulk reaction data confirm the interlocked nature of MINTs.

We will also show that the effect of the mechanical bond on the properties of SWNTs is unique, and clearly different from the noninterlocked, supramolecular compounds.³

References:

(1) a) de Juan, A.; Pérez, E. M. Nanoscale 2013, 5, 7141; b) de Juan, A.; Pouillon, Y.; Ruiz-Gonzalez, L.; Torres-Pardo, A.; Casado, S.; Martin, N.; Rubio, A.; Pérez, E. M. Angew. Chem., Int. Ed. 2014, 53, 5394; c) López-Moreno, A.; Pérez, E. M. Chem. Commun. 2015, 51, 5421; Leret, S.; Pouillon, Y.; Casado, S.; Navio, C.; Rubio, A.; Perez, E. M. Chem. Sci. 2017, DOI: 10.1039/c6sc03894h.

(2) a) de Juan, A.; Mar Bernal, M.; Perez, E. M. ChemPlusChem 2015, 80, 1153; b) de Juan, A.; Lopez-Moreno, A.; Calbo, J.; Orti, E.; Perez, E. M. Chem. Sci. 2015, 6, 7008.

(3) a) Martínez-Periñán, E.; de Juan, A.; Pouillon, Y.; Schierl, C.; Strauss, V.; Martín, N.; Rubio, A.; Guldi, D M.; Lorenzo, E.; Pérez, E.M. Nanoscale, 2016, 8, 9254; b) Lopez-Moreno, A.; Nieto-Ortega, B.; Moffa, M.; de Juan, A.; Bernal, M. M.; Fernandez-Blazquez, J. P.; Vilatela, J. J.; Pisignano, D.; Pérez, E. M. ACS Nano 2016, 10, 8012.